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Fourteen months ago all-star sports executive Tim Leiweke took over as president and CEO of Maple Leaf Sports and Entertainment and assumed a mandate as urgent as it was daunting.

Transform a corporation criticized by local sports fans over the perception that it prioritized making money over winning titles into a dynamic organization that focused first on championships — while making big money along the way.

Quickly, MLSE jettisoned incumbent executives such as COO Tom Anselmi, and shortly after major corporate partnerships materialized, like the one leading to a flagship Sport Chek store at Maple Leaf Square.

And by April the Raptors, remade under general manager Masai Ujiri, another Leiweke hire, had qualified for the playoffs for the first time since 2008.

Is two years enough time to turn around an organization as large as MLSE?

Experts say Leiweke has set the company up for long-term success, but that 24 months is just enough time for the superstar executive to leave his legacy in Toronto tantalizingly unfulfilled.

“Turning teams around on a one-season basis doesn’t mean he’s fulfilled his mandate here,” says sports industry consultant Brian Cooper, president of the S&E Sponsorship Group. “He made pretty good headway and he changed the culture. Broad scope leadership, he provided that.”

In Leiweke’s first six months on the job, MLSE rattled off a string of victories off the field. Leiweke signalled his intention to transform the organization and its biggest property, the Maple Leafs, from a national player into a global sports brand.

In early September 2013, MLSE finalized a comprehensive partnership with Canadian Tire, and by the end of the month it had signed hip-hop megastar Drake as the Raptors’ global ambassador. And in January, TFC paid $20 million in transfer fees to acquire a pair of soccer standouts — Jermain Defoe and Michael Bradley — who figured to vault the club into the playoffs.

And even in deals that didn’t involve Leiweke directly, executives credited the corporate culture he created.

“It’s no secret we’re looking to grow the company,” said MLSE chief commercial officer Dave Hopkinson in March, when discussing in-arena ads aimed at fans watching Leafs games in China. “Tim has challenged us to think globally.”

And while securing an NFL franchise wasn’t technically part of Leiweke’s role, he didn’t distance himself from the efforts of rock star Jon Bon Jovi and MLSE chairman Larry Tanenbaum to buy the Buffalo Bills.

“If down the road there’s something I can do to help on the NFL I will be prepared to use those relationships because now Toronto is my hometown,” said Leiweke in his May 2013 introductory conference call.

Leiweke’s camp insists the failure of the group’s bid for the Bills didn’t factor into the decision to leave MLSE next year. Instead, Leiweke always viewed his time in Toronto as two intense years spent turning the company around.

And when he leaves, expect franchise values for the Raptors, Leafs and TFC to take a small hit.

“There’s been a big spike (in the Forbes value) of MLSE clubs since Leiweke started. Unless they replace him with an equally competent CEO, it can have an impact on the value of the franchise.”

But franchise valuation expert Drew Dorweiler says the Raptors’ unexpected playoff run last season, coupled with a TFC club that appears set for its first post-season appearance, can also boost values.

Either way, O’Reilly says Leiweke has set MLSE up for long-term success even if he leaves earlier than first expected.

Between transfer fees, star player salaries and renovations to BMO Field, the company has committed roughly $220 million to TFC’s turnaround, while sponsorship staff are already in the habit of aggressively pursuing deals.

While Bell and Rogers remain communications and sports media rivals, the two companies that own the bulk of MLSE also are unlikely to alter Leiweke’s strategy, even after he leaves.

“They’re all aligned. They want to go bigger and be growing,” O’Reilly says. “I can’t imagine ownership going back to a more conservative, financially only focused goal.”

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